


Red Rose

by AnotherWorld3111



Series: Angels and Demons Verse [1]
Category: Supernatural
Genre: Alternate Universe - Assassins & Hitmen, Alternate Universe - Spies & Secret Agents, Anal Sex, Assassin Dean Winchester, Assassins & Hitmen, Barebacking, Bottom Dean, Bottom Dean Winchester, Bottom Dean Winchester/Top Sam Winchester, Dean in Panties, Gangs, M/M, Mafia Leader Sam, Mobs, Porn With Plot, Rough Sex, Top Sam, Top Sam Winchester, mafia, sensual kissing
Language: English
Status: Completed
Published: 2017-12-21
Updated: 2017-12-21
Packaged: 2019-02-17 23:46:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,544
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13087980
Author URL: https://archiveofourown.org/users/AnotherWorld3111/pseuds/AnotherWorld3111
Summary: Mafia Leader Sam L. Wesson. The most powerful man alive, the most feared, the most revered. No one ever dares question him, or hell, even go against him, not if they want to live. With a snap of his fingers, he could have anyone at his mercy.Dean S. Winchester. Best goddamn assassin in the entire planet, that anyone who finds themselves under his radar better make the best of their last moments, because for sure they’re not gonna live any longer. No matter what.But even the famed Dean Winchester should have known better to go against Sam L. Wesson. There’s a reason they call him ‘The Devil,’ after all.





	Red Rose

**Author's Note:**

> *mumbles* I apologize in advance for all the mistakes/typos  
> Here I was, tryna go to sleep, planning on waking up early the next day and all, when - BAM! This hits me, and I just had to get it out. Fuck my brain, fuck me, and fuck sleep

   The heavy metal door swung open, the creaking of its hinges echoing loudly within the room. A white shoe stepped inside, followed by its pair, and soon, a man clad in complete white save for the stark red rose in his pocket appeared, stepping into the morning light granted by the sole source from an overhead window. As his eyes roved over the man in front of him, the corners of his lips quirked up, until he was eventually chuckling.

   “Dean Smith Winchester.” The man dragged the words, his voice low as he stepped forward, grinning when he was only met with a haughty look in return.

   “Sam L. Wesson.” Dean returned, not looking the slightest bit disturbed, for all that he was chained to the ceiling and hence, for all intents and purposes, at the mercy of the man in front of him. “I’d shake your hand, but, I’m a bit otherwise occupied.”

   Sam chuckled again, taking a step back as he dropped his eyes. Clad in a black suit, despite being all rumpled up from the chains, Dean Winchester was still upholding his reputation for his snark, looking for all the world relaxed, despite his current situation.

   “I would shake your hand as well. After all, getting to meet the world’s best assassin is no small feat.” Sam acknowledged, starting to pace from side to side. And yet, his eyes never left Dean’s form. “It’s an honor, Dean, truly. To meet you.”

   Dean scoffed, raising an eyebrow, perfectly curved above the most beautiful eyes Sam has ever had the pleasure of laying his own eyes on. “Yeah. And yet...” his eyes darted around, for only the barest of a second, before he was looking back at Sam, the action so quick it would have been missed had Sam not been paying his utmost attention to the assassin. “You require eight armed bodyguards while meeting me. While I’m chained to the ceiling. I’ve gotta admit, I’m not really feeling the honor in return.” Dean retorted. “Admittedly, it took almost your entire group of our people to capture me, where I’ve showed my power by taking most of them down with me as well... and yet, I’m seeing none of all the mighty Sam in return. You know, the powerful mafia leader who’s supposed to be unbeatable and everything.” Dean snarked, a slight smirk edging its way on his lips. He huffed, swaying in the chains, the metallic links clinking in the background. “Where’s the big bad wolf at his worst, hm?” He goaded.

   All the while, Sam had been quietly listening, observing, taking in every word, every action coming from Dean. But with those words, he snapped.

   Striking forward, he was right in front of Dean in one step. One heavily landed blow later, he took another step until his chest was practically brushing against Dean’s, tipping his head down as he harshly yanked Dean’s head up by the hair, forcing the assassin to meet his eyes. Blood oozed down from the cut on his cheekbone, and Sam’s eyes were drawn to it, his thumb moving until he was pressing down on it, relishing in Dean’s hiss of pain.

   “Has no one ever taught you,” Sam whispered, his voice dark and threatening, only meant for Dean’s ears. “That you should never poke at a snake?”

   Dean’s jaw clenched, meeting Sam’s gaze defiantly despite the monetary flash of pain as Sam pushed harder against the thumb. But as soon as it came, it was gone, and Sam lost his patience.

   “Everyone out!” Sam barked, letting go of Dean none too kindly, watching as Dean’s head dropped in surprise, caught off guard when Sam unexpectedly let him go. He took a step back, and then another. “I want to show this man what happens when he stupidly steps right into The Devil’s lair.” He never took his eyes off of Dean, even as he started circling Dean. Right as he was behind the assassin, he realized that none of his men had moved, and with a pointedly raised eyebrow, his right hand man, Azazel, stepped forward.

   “Sir, you shouldn’t be left alone with him, he’s highly dangerous-“

   “He’s chained. To the ceiling!” Sam snarled. “And even then, do you not trust your leader?” Not giving a rapidly paling Azazel a chance to reply, Sam stepped forward, bringing himself closer to Dean’s back. “Get out. Now!” He roared, and instantly, everyone snapped, getting into action. Sam watched with satisfaction as one by one, each of his men left the cell, after respectably bowing to him before turning their backs on him. Azazel was the last to leave, casting Dean one last look filled with mistrust and disgust, before he too bowed as well to Sam, and then left.

   The door shut with a clang in front of them.

   And then Sam was pressing himself to Dean’s back, his breathing already heavy as Dean let out a gasp, arching his back before pressing himself into Sam’s body behind him.

   “I thought you’d never make them leave.” Dean moaned as Sam nibbled on his ear, hands urgently working at Dean’s belt, tugging it off with harsh movements. His Dean may have looked absolutely delectable in this suit, but never had Sam loathed whatever Dean may wear - for all that he might have loved it seconds before - when he was trying to remove it from his Dean’s body.

   “I’m afraid we don’t have much time.” Sam whispered, right in Dean’s ear, his breath a hot puff against Dean’s skin. He unzipped Dean’s pants, and quickly pushed it down, groaning when hands met the lacy black of the panties covering Dean’s ass. “As much as I want to take my time absolutely ravishing you,” Sam hissed, biting and pulling at Dean’s ear with his teeth before continuing, his hands massaging Dean’s cheeks. “We’re going to have to make this quick.” Sam quietly bemoaned, his voice filled with regret.

   Dean let out a breathy exhale, his head dropping back until it was resting on Sam’s shoulder, pushing his ass back into Sam’s hands. “Already lubed myself.” Dean moaned, his voice high and cracking as Sam teased at Dean’s hole through the panties, to find in fact, that Dean had lubed himself, judging by the slightly wet material right at Dean’s loose hole. “Wanted to be wet and ready for you.”

   Sam groaned, his finger automatically shoving into Dean’s hole at that, dropping his own head on Dean’s shoulder as Dean gasped again, let out a slight whimper at the end when Sam added another and crooked his fingers, the panties still separating their skin from making contact.

   “My Dean.” Sam whispered, pulling his fingers out, pushing the panties aside only to push his fingers back in, thrusting a few times before adding another finger. “So good.”

   Dean’s eyes, long ago having fluttered closed, was now scrunched shut, his hips moving back in an effort to push Sam’s fingers deeper inside. Sam swallowed, pulling his fingers back out ever so tauntingly slow. “Yes,” Dean whispered. “So good for you, Sammy. So good for you,” Dean whined, impatient as his hips pushed back more urgently. “God, please. Please, fuck me.”

   Sam groaned, and the very next second his fingers were instantly out, hand grappling for his zipper before he finally managed to open it, taking out his long, hard cock into his hand. “You want me to fuck you, Dean?” Sam whispered, bringing his head back to be able to look at Dean’s face. “You want my thick cock in you?” Dean moaned, his head bobbing up and down in a visible yes. Above them, his hands gripped tighter on the chains encircling his wrists, and probably the only thing - apart from Sam - right now, holding him up. “Then open your eyes. Open your gorgeous eyes for me, Dean. Look at me, beautiful.” Sam pressed.

   Only the briefest of seconds passed before Dean obeyed, and the moment the mesmerizing green of Dean’s eyes were focused on him, facing him as much as he could by twisting his head as far as possible so he could look at Sam when he was behind Dean, Sam pressed his cock to Dean’s hole, rubbing at his taint, but not pushing inside. Not yet. “God, I love you.” Sam murmured, pressing a kiss to the corner of Dean’s lips, a smile immediately blooming on his own when Dean hungrily leaned close to him for more. Obliging, Sam leaned forward as well, until his lips were brushing against Dean’s, the soft, plump skin, wetting from their saliva mixing, making Sam’s head spin.

   “I love you too, Sammy.” Dean whispered, the moment they had paused to take a breather. But the moment those words had escaped Dean’s lips, Sam was surging forward again, and doing so, he pushed into Dean, bottoming in one smooth thrust.

   Dean pulled away, facing forward but head dropping against Sam as he momentarily tensed, before just as quickly relaxing, loose limbed against Sam as Dean completely and utterly let Sam take over.

   He started out slow, hating the feeling of pulling out from Dean, but with each thrust, his speed increased, until Sam was absolutely slamming into Dean, hands leaving their place from gripping Dean’s hips until Sam was instead wrapping his arms around him, holding Dean close to his body as he roughly took what he wanted. But one of his hands nonetheless crept down, moving until it and into contact with Dean’s cock, still covered by the lacy black panty. Not even bothering to move it out of the way, Sam fondled Dean’s cock, stroking and rubbing and just losing himself in Dean’s guttural moans, the clanking of the chains above them growing louder and louder as Sam thrusted harsher and faster, as Dean grew more and more desperate and started to completely rely on only Sam and the chains to keep him even vertical.

   “God, Sam, Sammy,” Dean blubbered, eyes fluttering but then focusing on Sam when he shot him a pointed glare, the heat of it immediately disappearing when Dean looked back at him, melting into something softer as Sam started peppering kisses all over Dean’s face. “Sammy, I’m so close-I’m about to-about to come-“

   “Come for me, my Dean.” Sam whispered, moving his hips even more so roughly, skin slapping against Dean’s pert ass, hand now working furiously at Dean’s clothes cock. “Come for me.”

   With a yell, Dean came, back arching as his cock spurted cum, staining the panties. He moaned when Sam still refused to stop moving his hand, smearing Dean’s come all over the front of his panty and his cock. His own hips stuttered as Sam came, and he bit down harshly against Dean’s bared neck, muffling his groan as he spilled his seed within Dean.

   Dean was whining, whimpering at the overstimulation against his sensitive skin, at the sting of Sam’s teeth embedding itself into his skin. When Sam came to, he let go, licking at Dean’s neck apologetically, giving Dean’s cock one last stroke before letting it fall limply between his thighs. Moving his hips backwards, Sam let out a small smirk at the squelching noise the action provoked, smirk only growing when he knew that despite wincing from the slight twinge of pain, Dean was still rolling his eyes at Sam.

   Hand still smeared with slight come, Sam pulled it back, pushing and tugging at the panties until it was covering Dean once again, before wiping his hand on it. Dean jumped, startled, but then huffed, resigning himself to Sam’s mercy.

   But Sam was done, and he pulled back, his other arm loosening but not completely letting go of Dean’s torso, as he pulled Dean’s pants back up his legs, purposefully trailing his fingers over the bare skin before covering them. Dean shivered at the contact.

   “I’ve got enough intel on Alastair.” Dean muttered, easily tilting his head to the side as Sam pressed a kiss on his shoulder there, hands moving back to the front to zip Dean up for him, making sure he didn’t accidentally get Dean’s dick in the way either. “All we need is one more sample for evidence, which is coincidentally in your office, and I can get my boss to either put a pin on his head, or put him away. Probably the former, though. For all his flawed righteousness, the man has absolutely no tolerance for sexual assault under the name of sex work.” Sam hummed, hands reaching up to start working at the chains around Dean’s wrists.

   “I suppose you should be getting to it then.” Sam murmured, pressing another kiss to the side of Dean’s forehead, smiling when he caught a glimpse of Dean’s eyes fluttering closed at the soft contact, and pressing himself closer to Sam. “Get advantage of me when I’m least expecting it and all.” Sam mentioned, his tone casual.

   The chains fell free, and instantly Dean whirled around, pressing himself bodily against Sam, looping his arms around Sam’s neck as he dragged him down to land sloppy kisses on Sam’s lips. If possible, Sam’s grin only grew wider, his hands falling back down to grip at Dean’s hips, fingers grazing at the edge of the panties peeking up from Dean’s waistband. His head tilted forward and down as he pressed his chest harder against Dean’s, meeting Dean’s kisses with just as equal fervor, rubbing his tongue against Dean’s, losing himself in Dean’s soft gasps and breathy noises.

   “Of course.” Dean muttered, seconds, minutes, hours later, the two of them breathing heavily, their lips still brushing against each other’s as Dean spoke. “You really should have been paying better attention, Sammy. Trained assassin and all, they’ll always be looking out for your weak spots. I mean, really. How could they even dare to think that they could capture the greatest assassin alive - Dean Winchester! Hm?”

   Sam hummed, grin never leaving his lips as he dug his fingers harder into Dean’s hips, knowing and not caring that there’ll probably be bruises there later. Dean’s legs spread further apart, Sam easily being able to tell that they were on the brink of just jumping up and patching themselves around Sam’s hips, and doing nothing to stop it. “Just like you’re the best at your job, I’m also the most fearsome leader, Dean.” Sam needlessly reminded him. “I don’t have any weak spots, Dean.” He spoke over Dean’s chortles, Dean’s amusement nonetheless rubbing off on Sam. “Not that anyone knows of.”

   “Sure.” Dean replied, landing an indulgent kiss on Sam’s lips, before moving his face so that his lips were brushing against Sam’s cheeks, one of his hands meanwhile coming down to finger at the now crumpled rose at Sam’s pocket. Ignoring one of Sam’s own hands coming up to cradle his face, gently swiping away the blood drying on his cheek there, Dean moved steadily closer to Sam’s ear as he lowered his tone, until Dean was speaking in a mere whisper, their secret hushed dangerously between them in the darkest of places, the darkest of moments, but the source of the lights within their core, bringing the two ever so closely together, forever.

   “But they’re not me. Are they, little brother?”

**Author's Note:**

> Hope y’all enjoyed, cuz I sure as hell did!!!
> 
> Check me out on tumblr?  
> @openharborbringontheships  
> I swear I won’t bite. Please, feel free to come over!


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